Dichloromethane → 2-Pyrrolidinone, 3-chloro-4-(chloromethyl)-1-(phenylmethyl)-

HRID 1111861Notes

Reaction equation

HRID 1111861 reaction equation
[CH2:1]([N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:9])[CH:6](Cl)[Cl:7])[CH:2]=[CH2:3].COCCOCCOC.N1CCCC1=O.C(Cl)[Cl:33]>>[CH2:10]([N:4]1[CH2:1][CH:2]([CH2:3][Cl:33])[CH:6]([Cl:7])[C:5]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8150DiglymeHCID 120252-PyrrolidoneHCID 10083827Acetamide, 2,2-dichloro-N-(phenylmethyl)-N-2-propenyl-

Product 1

HCID 118212562-Pyrrolidinone, 3-chloro-4-(chloromethyl)-1-(phenylmethyl)-

Procedure

Eleven and one-tenth grams of N-allyl-N-benzyl dichloroacetamide was dissolved in 12 ml. of diglyme and 1 g. of anhydrous ferrous chloride added. The mixture was heated at reflux under nitrogen until conversion to the pyrrolidinone was complete as indicated by GLPC. The mixture was diluted with methylene chloride, washed with 5 percent hydrochloric acid, separated, dried over anhydrous magnesium sulfate, treated with activated carbon and Florisil and stripped under vacuum. Yield was 6 g. of the title compound, nD30 1.5387.

Workup

  1. temperatureThe mixture was heated
  2. washwashed with 5 percent hydrochloric acid
  3. customseparated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with activated carbon and Florisil

Sources & evidence

ORD record
ord-5f883e302c4a4256a63feae086771481
Source dataset
uspto-grants-1978_10
Patent number
US04119636

Reaction notes

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